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I am using Microsoft Outlook 2016 MSO (16.0.9126.2315) 32-bit by way of my company Microsoft Office 365 ProPlus account.

The default handling of outgoing e-mail messages, regardless of type, is such that a copy is saved to the Sent Items folder which is fine in almost all cases.

With respect to conversations, however, an issue arises when the Sent Items folder is purged via the Delete All action. All my contributions ( replies ) to the conversation are lost, as you would expect.

The desired behavior would be to have my replies to conversations save to the folder where the conversation lives instead of the Sent Items folder, preventing this data loss from occurring.

Is this possible within Outlook or Office 365?

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See here for the support page that shows the option.

Basically:

Change where sent email messages are saved when using an Exchange account

Click File > Options > Mail.

Under Save messages, make sure the Save copies of messages in the Sent Items folder check box is selected.

Select the When replying to a message that is not in the Inbox, save the reply in the same folder check box.

  • I had already made those changes. Interesting. To be fair, most of my testing was from within the Inbox and the option specifically states not in the Inbox. That works as intended. However, I'm still left with the undesired behavior for conversations in the Inbox. – Code Maverick Dec 18 '18 at 20:14
  • You can create rules to move them to other folders as they arrive. I do this to organize in-house departments, clients, etc. Depending on the size of your org./clientele. I do this so that anything that remains in the inbox is either garbage, or something new that I need to check on, but is not a priority. – BlueGI Dec 18 '18 at 20:20
  • I do that as well ( or at least I try to ). Every attempt to achieve Inbox Zero, though, usually ends up OBE'd. I appreciate the response. – Code Maverick Dec 18 '18 at 21:12

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